Top Five – Windows Operating System Releases

So, with a new Windows operating system out for a few months, a new blog that needs content, and, specifically, a Top List category that needs a starting post, I decided to start with my Top Five Windows Operating Systems. Also, just for clarification, I do want to say that this isn’t a Pro-Microsoft post, as much as it may feel like it. I firmly believe that all operating systems are made to be equal, and different types of operating systems (Linux, Mac OS, Server Systems) all have their pros and cons, this was just my first thought for this category.

Also, please bear in mind that the positioning on this list is my personal opinion on these operating systems and does not reflect the stability, functionality or my recommendation on which operating system to have on your system. For the record, if you have a system that’s capable enough to run Windows 7 or Windows 10, those would be the two I recommend.

In addition, I did not give any consideration to Windows 10 for this list as, since it is such a new operating system still, I haven’t had adequate time to judge it fully. So, let’s start this list!

5. Windows 3.1/For Workgroups 3.11Windows31

Released: April 6th, 1992

This was the my very first interaction with the Microsoft Windows platform. My first computer, I was running Windows for Workgroups 3.11. Windows 95 was a little to new to be running on a 10 year old’s computer and so this is what I had; and I absolutely loved it.

One of my favorite features of Windows 3.x is the fact that, technically speaking, it wasn’t even an operating system – it was a menu system. Once the Operating System booted (MS-DOS specifically in my case) you had complete access to the system from the command line – which I still highly prefer today – but once you were done, or if you preferred a GUI, you just type WIN and there it was in all of its 16 bit glory.

If you had the “For Workgroups” version, you had a bit of better networking functionality and it’s the version I like to play around with the most to this day. It was probably more difficult back then, but it’s always fun to get a Windows 3.x machine on my network and go visit Facebook or Google with Internet Explorer 3.

To be honest, the reason why it’s at #5 and not #1 is because there is absolutely no way for me to efficiently use this operating system today. If Microsoft were to revamp this version of Windows, make it 64 bit compatible, and re-release it – I would definitely use it, Program Manager and all!

4. Windows 98 SEWindows98

Released: April 23rd, 1999

This was a bit of a tossup between Windows 98 SE and Windows ME – just kidding! But it was a tough choice with Windows 95. Windows 95 is what essentially started the interface that we all know and love today (except Windows 8 – the black sheep) and I feel it at-least deserves a shoutout for that.

Windows 98 SE (make note that I’m not forgetting the SE part) however took what Windows 95 did, and simply just made it better. We were no longer bound to static images for our background – which paved the way to the family slideshows we all have now – and, even though it felt almost the same as Windows 95, it was just a whole lot cleaner.

In addition, one of the biggest reasons why this took this spot before Windows 95 is because this is where I started my gaming life. Age of Empires, Dark Age of Camelot, StarCraft and many others made their way into my life because of this old friend.

My final reason as to why 98 SE made the list is because this is where VICKI got her name. Long story short, I name my computers. It’s weird but I look at it like this – people name their cars and some pets are treated a lot better than some humans. I’m not talking down about either of those things but, considering that, I think that naming my computers isn’t that big of a deal.

3. Windows 8 (8 and 8.1)Windows8

Released: October 26th, 2012

So I feel that I may get a little bit of grief for including Windows 8 on my top 5 list, especially because it’s in the top 3. Most of that grief would be the reason though: Cloud accounts and Start Screen – but let me explain!

Windows 8 could very well be Microsoft’s most ambitious operating system. There were several big goals that Microsoft was trying to accomplish with this release, two of which (as stated before) are why Windows 8 made my list. Let’s start with Cloud Accounts.

Now, to be clear, during the release of Windows 8, I found Cloud Accounts absolutely pointless – until I actually used them. It was quite nice to have a similar experience on all of my Windows 8 devices. My wallpaper, histories, bookmarks, application data and much more data automatically transferred between my desktop and laptop which turned out to be really nice. Sometimes, my son plays on my computer and I still need to get work done, so I’ll work on my laptop. With Windows 7, it was just my Google content that synced (as I stayed signed into chrome) and I can’t recall how many times I’d let my son jump on my computer, only to realize I need to jump right back on to find a website I was referencing or copy some data to my Google Drive, just to use it on the laptop. With the cloud, I can start on my desktop and continue working on my laptop. It was a very nice way for device unification, for me anyway.

Speaking of “device unification”, that brings me to my next reason: The Start Screen – which I have a very strange love-hate relationship with it. I didn’t have any touch screen monitors so, even for me, navigating through the touch-optimized environment for Windows 8 was extremely clunky. I was able to bypass a lot with keyboard shortcuts but some I just couldn’t. This was a huge reason as to my original distaste of Windows 8, until I repaired a touchscreen laptop running Windows 8, for the first time, and I absolutely loved it. A little later, I had access to Windows 8 tablets and phones and, while it wasn’t the exact same, I understand what Microsoft was trying to do; one experience across multiple devices.

I had two primary complaints with Windows 8 however, and they are both the same reason Windows 8 won #3 on this list. First of all, regardless of the hardware you had in your machine, or its touch capabilities (or lack thereof possibly), you were stuck with the Start Screen. Sure, there are options such as Classic Shell and Start 8 which would give you the “Start Menu” experience, but it wasn’t actually a part of the operating system. That combined with Microsoft boasting the return of the Start Button in 8.1, only to have it map to the screen that everybody already despised, did not help the situation.

Secondly, and unfortunately this trend followed with Windows 10, many people felt they were forced into creating a Cloud account (once again, I’m looking at you 8.1). During installation, there’s a little bit of text on the bottom left hand side of the screen which says something along the lines of “Sign In with a Local Account instead” which allowed you to bypass it, unless you were running 8.1, at which point you had start the Cloud Account creation process before you would be presented with the option. In both cases, the bit of text, which wasn’t even a button – just a link on the screen, was displayed in such a way that it was very easy to miss. This is a trick many websites and other pieces of software use to try to trick people to purchase their software or services and so, when I saw this being practiced by a corporation as large as Microsoft, it really got under my skin.

2. Windows 7Windows7

Released: October 22nd, 2009

As we near the end of this list, the more nostalgia I feel for a lot of these past operating systems, what they’ve helped me accomplish, and how radically far the Windows operating system has evolved it’s first release (which, coincidentally, was 5 days before I was born). Now we are at, where many people that I’ve spoken to agree, is the best operating system that Microsoft has ever launched.

A lot of what made Windows 7 great could have been the fact that it was following the release of Vista, but to me there was more than that. In my experience, Windows 7 seemed like the first complete operating system that Microsoft had ever released. With a lot of previous versions, Microsoft created what they claimed to be a complete operating system, only to release service packs or updates that altered the system later. Now, while Microsoft did release SP1 some time after, it’s still a completely usable operating system without it.

In addition, Starting with XP, and heavily followed up with Vista, Microsoft had already made their operating system “Pretty”. They took away the traditional GUI look and feel, gave it some curves, translucency and effects and, while they did improve more upon the look in Windows 7, they seemed to focus more on stability, functionality and ease of use; and I know I’m not the only one who feels this way, statistically speaking anyway. Before the mainstream use of Windows 7, a lot of calls I received went along the lines of “I’m running Windows <Insert Version Here>, How do I do this simple thing?”. Afterwards, those calls became less and less frequent and I love seeing how happy people become when they finally understand how to use their computers.

1. Windows XPWindowsXP

Released: October 25th, 2001

Now, as I said, many people agree that Windows 7 was the best release of Windows, but I don’t. Sure, Windows XP was incredibly shaky at launch, but they fixed it. The first improvement, I’ve already stated, it’s the fact that it was pretty. Windows 1.* and 2.* were high contrast messes, out of necessity; Windows 3.x looked better, and 95 through 2000/ME looked virtually the same, just had more customizable options and the colors were slightly altered in each new version. Windows XP though, you had Bliss; You had a fun new login screen; you had the expanded start menu; and you had better themes.

It was so stable too… Once again, not at first, but later. Windows XP Service Pack 3 is by far my favorite update to my favorite Windows operating system and the introduction of all the various superuser tools just made life easy.

And finally, a single Windows distribution. Before XP, each iteration of Windows essentially had two versions – one for home and one for business. Although you could say it was pretty much the same (XP Home and XP Pro), they were both the same Windows product, while Windows 2000 and Windows ME were two separate products. This solved so many headaches and security concerns as everything was built from the same NT kernel, providing streamlined security updates.

I didn’t list any cons with Windows 7, but I do have a few gripes here. How this still made #1 – it was just that great, in my honest opinion.

First complaint: You only had the three colors: Blue, Olive and Silver (my personal favorite). I really wanted to make my own scheme this way. It was possible, but I couldn’t figure out how to do it. And, yeah, you could switch back to the old style of the GUI, but that took away some of the cool stuff.

Second Complaint: Upgrade didn’t work properly (and sometimes still doesn’t work in Windows 10). When Windows XP launched, I was running Windows 98 SE and bought an upgrade copy for Windows XP Home (I should have went full Pro). I could barely use the operating system. I ended up shelling out for the full version of Windows XP Pro, which was expensive for a 16 year old I might add.

Bonus – Bottom of the Barrel: Windows VistaWindowsVista

Released: January 30th, 2007

What could I possibly say about this …version? This is my favorites list and, when I started writing it, I thought it’d be fun to throw this on here and do this quick synopsis, but I can barely think of a single thing to say… It was “pretty” I guess.

I know people that like to still use Vista and, as an operating system, it was a great piece of software. It provides all the essential functionality of an operating system plus some and, if you never had an issue with Vista, I can definitely see why someone would like this one, but I just didn’t. This was about the time that I had actually realized what I feel the secret plan for Windows is from Microsoft:

Windows 3.x came out in 92 and Windows 95 launched in…1995. These were both good versions of Windows. Yes, 95 was a quite buggy, but in my opinion, the pros outweighed the cons. Windows 98 launched in (surprise) 1998, and it was abysmal and was barely just an enhanced version of Windows 95. 98 SE came out, which I always kind of refer to as a Service pack more than an OS on its own, so I strike that from this theory on that reason, and to make the secret plan true of course. Next was Windows 2000 in early 2000, which was just great, then came Windows ME in late 2000 which… yeah… Then came XP in 2001 (#1 Windows OS award), followed by Vista (bad), then 7 (great), then 8/8.1 (statistically bad) which now we’re at 10, which looks like it may be tipping towards good.

I need to find a quicker way to explain that but to sum it up, I think Microsoft has, for a long time, had a secret plan to release a bad operating system after a good one, just to get feedback on how to make another good one. Yeah, that’s totally what’s going on…


So that’s it for my list. Do you agree? Disagree? Was I too wordy? Not descriptive enough? Feel like I’m an idiot? Spot an error? Leave a comment and let me know, I’m always happy to interact with my visitors!

Leave a Reply

Your email address will not be published. Required fields are marked *